Triazolopyrimidines

Abstract

Novel triazolopyrimidines of the formula in which R 1 represents amino, represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylamino, dialkylamino, alkenylamino, alkynylamino, cycloalkylamino, N-cycloalkyl-N-alkylamino, alkylideneamino or heterocyclyl, and R 2 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted heterocyclic ring, R 3 represents aryl which is optionally mono- to tetrasubstituted, R 4 represents halogen, cyano or represents in each case optionally substituted alkoxy or dialkylamino and X represents halogen, a process for preparing these novel substances and their use for controlling unwanted microorganisms. Novel intermediates of the formulae and processes for their preparation.

1 . Triazolopyrimidines of the formula  
     
       
         
         
             
             
         
       
       in which  
       R 1  represents amino, represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylamino, dialkylamino, alkenylamino, alkynylamino, cycloalkylamino, N-cycloalkyl-N-alkylamino, alkylideneamino or heterocyclyl, and  
       R 2  represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or  
       R 1  and R 2  together with the nitrogen atom to which they are attached form an optionally substituted heterocyclic ring,  
       R 3  represents aryl which is optionally mono- to tetrasubstituted,  
       R 4  represents halogen, cyano or represents in each case optionally substituted alkoxy or dialkylamino and  
       X represents halogen.  
     
   
   
       2 . Process for preparing triazolopyrimidines of the formula (1) according to  claim 1 , characterized in that 
 (a) dihalotriazolopyrimidines of the formula                          in which    R 3 , R 4  and X are as defined above and    Y 1  represents halogen,    are reacted with an amine of the formula                          in which    R 1  and R 2  are as defined above,    if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.    
   
   
       3 . Composition for controlling unwanted microorganisms, characterized in that it comprises at least one triazolopyrimidine of the formula (I) according to  claim 1 , in addition to extenders and/or surfactants.  
   
   
       4 . Use of triazolopyrimidines of the formula (I) according to  claim 1  for controlling unwanted microorganisms.  
   
   
       5 . Method for controlling unwanted microorganisms, characterized in that triazolopyrimidines of the formula (I) according to  claim 1  are applied to the unwanted microorganisms and/or their habitat.  
   
   
       6 . Process for preparing compositions for controlling unwanted microorganisms, characterized in that triazolopyrimidines of the formula (I) according to  claim 1  are mixed with extenders and/or surfactants.  
   
   
       7 . Dihalotriazolopyrimidines of the formula  
     
       
         
         
             
             
         
       
       in which  
       R 3 , R 4  and X are as defined above and  
       Y 1  represents halogen.  
     
   
   
       8 . Process for preparing dihalotriazolopyrimidines of the formula (U) according to  claim 7 , characterized in that 
 (b) dihydroxytriazolopyrimidines of the formula                          in which    R 3  and R 4  are as defined above    are reacted with halogenating agents, if appropriate in the presence of a diluent.    
   
   
       9 . Dihydroxytriazolopyrimidines of the formula  
     
       
         
         
             
             
         
       
       in which  
       R 3  and R 4  are as defined above.  
     
   
   
       10 . Process for preparing dihydroxytriazolopyrimidines of the formula (IV) according to  claim 9 , characterized in that 
 (c) arylmalonic esters of the formula                          in which    R 3  is as defined above and    R 5  represents alkyl having 1 to 4 carbon atoms    are reacted with aminotriazoles of the formula                          in which    R 4  is as defined above,    if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.    
   
   
       11 . Aminotriazoles of the formula  
     
       
         
         
             
             
         
       
       in which  
       R 6  represents cyano or bromine.  
     
   
   
       12 . Process for preparing aminotriazoles of the formula (VI) according to  claim 11 , characterized in that diaminotriazole of the formula  
     
       
         
         
             
             
         
       
       is initially diazotized and then reacted with a brominating agent or a cyanating agent, if appropriate in the presence of a diluent and if appropriate in the presence of further reaction auxiliaries.